While hip hop isn’t as geographically divided as it once was, certain cities can still be territorial in terms of ownership of sounds and styles. For years now, Milwaukee and Detroit have shared similar, yet different ideologies, but when one of their biggest current rap stars came to Summerfest on Saturday night, he felt right at home.

On the final night of Summerfest 2025, Tee Grizzley took to the Generac Power Stage, capping off a day full of buzzworthy Midwest rap that also featured Milwaukee’s own 414BigFrank and SteveDaStoner. There was high humidity and rain in the forecast, but the elements didn’t stop a massive crowd from congregating all the way to the main stretch of the festival grounds, akin to some of the most notorious shows in recent Summerfest history. 

WIth fans packed into the barricades as much as physically possible, they were hyped from the moment that opening tracks dropped from DJ Ace. By the time the main attraction made his way to the stage, things were at a fever pitch. He quickly went into a few bars of “First Day Out,” the song that broke him and his most successful track, with the crowd screaming along every bar. It was just a temperature check, though, with the full song coming later on in the night.

For the rest of his 45 minute headlining slot, there was no chill from the crowd any time that Grizzley would go into another song. Everything was met with a warm response, including material from “Forever My Moment,” a project that dropped this past May. 

“It damn near feels like I’m at the crib” he told the Milwaukee crowd. “This 313 to the 414 thing is real. It feels like home.” Of course, that got a reaction, right before going into “Colors,” which had the bleachers bouncing even more.

Legal drama is certainly central to Tee Grizzley’s story, and while he has plenty of material of his own, his ceded time in his set to shout out fellow rappers currently incarcerated. That meant dropping tracks like “Young Grizzley World” with YNW Melly and “Back In Blood” from Pooh Shiesty. He would run through four tribute tracks before getting back into tracks where he was the main artist.

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Grizzley also wouldn’t have to do much on stage to get the crowd to respond to him. His delivery is charismatic enough to have you hooked on his songs, and the Midwest underground feel to his beats hit hard enough to rattle the railings and bleachers of the Power Stage with every bass drop. While Grizzley calmly walked the stage and delivered his bars, either side of the stage had someone from his circle with steam cannons on a handheld hose. At one point, Tee himself would take the steam cannon to spray the crowd in the pit, but it was mostly out of steam at that point. 

When Tee himself was out of steam, though, he had backup. About halfway through the set, the rapper would walk next to DJ Ace’s riser to dry his face and take a breather. While that happened, though, the Grizzley Gang, aka a set of four dancers would take center stage to keep the crowd energized. With a set length that has been common for Summerfest rap acts, but short by overall festival standards, it felt awkward to see him take a pause in the middle of his set. While he was taking a break, though, the crowd definitely was not any time soon.

Once we were back to regularly scheduled programming, Tee was back in full force, dropping some of the biggest crowd favorites. “Loophole,” a track that features 21 Savage, got an especially loud reaction, and he would bring things down for the ladies on “IDGAF” that features Chris Brown and Mariah The Scientist. The female contingent of the Generac Power Stage crowd was especially vocal for Mariah’s verse. 

Things would pick up once again for “Gorgeous,” a track featuring Skilla Baby, and during the song, a stool would be brought out for Tee to take things home for the night. He had one more message for the crowd, telling Milwaukee that he had no idea that the song he was about to drop was going to change his life. That, of course, was the lead in to the full version of “First Day Out,” which then got ran back without the beat, and thousands of people to scream the verse along with him. DJ Ace would play him off, before promoting that that after party was headed to Room Seven to finish the night.

While Tee Grizzley got in and out in a tight 45 minute set on Saturday, the crowd stayed as hot as the summer weather for him throughout the show. Milwaukee isn’t officially home for him, but he certainly claimed it for the night, as much of the Midwest continues to proudly claim him as one of their own.